Penetrative actions play a crucial role in determining success in football. The aim of this study was to quantify the association between penetrative actions and match outcomes at the 2022 FIFA World Cup. Statistical analyses were conducted on 59 matches decided within regular time. The generalised linear mixed model (GLMM) and magnitude-based inference (MBI) were employed to examine the association between various penetrative action parameters and match outcomes (win/draw/loss) at both between- and within-team levels. The results showed that differences in penetrative actions between teams did not yield clear differences in winning probability (all likelihood effects < 95%). However, a two-within-team standard deviation (SD) increased in (i) attempted line breaks, (ii) completed line breaks, (iii) attempted line-breaking passes, (iv) attempted overthe-top line breaks, and (v) completed over-the-top line breaks raised a team’s probability of winning by 34.3% (90% CI±15.1%), 30.8% (±14.6%), 33.8% (±15.1%), 34.8% (±15.0%), and 38.2% (±15.5%), respectively. When playing against opponents utilizing a three-line defensive structure, a two-within-team SD increased in (i) attempted line breaks, (ii) attempted line breaks within the opponent’s formation, (iii) attempted final defensive line breaks, (iv) attempted second defensive line breaks, and (v) completed second defensive line breaks elevated the winning probability by 34.0% (±14.4%), 32.0% (±14.6%), 29.4% (±14.6%), 37.9% (±14.5%), and 33.3% (±14.4%), respectively. It is concluded that penetrative actions demonstrate a clear positive association with within-team winning probability. Different types of penetrative actions were associated with different levels of winning probability. The association between penetrative actions and winning probability varies across tactical contexts. These findings provide practicable insights for optimising offensive strategies in elite football.